Heretofore, reports have been documented on many asymmetric transition metal complexes as catalysts for asymmetric catalyst reactions, and a number of asymmetric ligands therefor have been developed.
Many of the asymmetric ligands are asymmetric diphosphine compounds represented by 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), and they are reported to achieve extremely superior selectivity and yield particularly in asymmetric hydrogenation reaction. However, application to asymmetric reactions other than the asymmetric hydrogenation reactions of asymmetric transition metal complexes using these asymmetric diphosphine compounds is limited. While application to the asymmetric cyclization reaction, asymmetric aldol reaction and the like has been reported (The Journal of Organic Chemistry, 2000, vol. 65, p. 5806-5816; Journal of the American Chemical Society, 2000, vol. 122, p. 4528-4529; Tetrahedron Letters, 2000, vol. 41, p. 891-895; Synlett, 1999, vol. 5, p. 605-607; Tetrahedron Asymmetry, 2000, vol. 11, p. 3561-3568), selectivity and yield are not entirely sufficient. Particularly, application to asymmetric addition reaction, asymmetric conjugate addition reaction and asymmetric hydroboration reaction highly useful as asymmetric reactions is not entirely sufficient in the selectivity and yield, and applicable substrates are limited.
Tetrahedron Asymmetry, 1993, vol. 4, pp. 743-756 discloses, as a monophosphine ligand for an asymmetric transition metal complexes, 1-(2-diphenylphosphanylnaphthalen-1-yl)isoquinoline (hereinafter sometimes to be abbreviated as QUINAP), and it has been reported that an asymmetric transition metal complex having QUINAP as a ligand catalyzes, with high selectivity, an asymmetric hydroboration reaction (Journal of the Chemical Society, Chemical Communications, 1993, p. 1673-1674) or asymmetric addition reaction of alkynes to enamine or iminium ion (Angewandte Chemie International Edition, 2002, vol. 41, pp. 2535-2541 and Angewandte Chemie International Edition, 2003, vol. 42, pp. 5763-5766), which are difficult by the use of BINAP etc.